Sodium Hydroxide → HCID 19099269, compound

HRID 1975460Notes

Reaction equation

HRID 1975460 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH3:13])[CH2:10][NH2:11])=[O:6])[CH:2]=[CH2:3].Cl[C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24].[OH-].[Na+]>O1CCCC1.O>[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([CH2:10][NH:11][C:23]([O:25][CH2:26][CH:27]=[CH2:28])=[O:24])[CH:12]([O:14][Si:15]([C:18]([CH3:20])([CH3:19])[CH3:21])([CH3:16])[CH3:17])[CH3:13])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 190993162-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine

Product 1

HCID 19099269HCID 19099269, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 11.4 g of crude 2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butylamine in 67 ml of tetrahydrofuran and 56 ml of water was added 2.8 ml of allyl chloroformate dropwise, while keeping pH 8-8.5 with 4N sodium hydroxide solution. The reaction mixture was extracted three times with chloroform, and the combined organic layer was washed with brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent followed by column chromatography on silica gel (hexane:ethyl acetate=1:1) gave 5.34 g of 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)- 3-t-butyldimethylsilyloxybutane.

Workup

  1. extractionThe reaction mixture was extracted three times with chloroform
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f8b7f4f6c2f340a086a35b66ca2b4f36
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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